


Winner Takes All

by IcyCryos



Category: Teen Wolf (TV)
Genre: Bottom Derek Hale, Drugged Sex, Dubious Consent, First Time, M/M
Language: English
Status: Completed
Published: 2018-09-29
Updated: 2018-09-29
Packaged: 2019-07-20 10:47:24
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 3,145
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16135661
Author URL: https://archiveofourown.org/users/IcyCryos/pseuds/IcyCryos
Summary: Desperate for the money for his hospitalized sisters, Derek falls into a dark web of unsanctioned fights where the winner takes all.





	Winner Takes All

**Author's Note:**

> Please be warned about the content of this story. It is VERY DARK and GRAPHIC. If you do not want to read anything regarding dubious consent or drugged sex, then please do not read any further. If you do choose to read further, then it is of your own volition and regardless of the warnings given.  
> **********  
> This is a work of fiction. Anything in this story is fictional. I do not advocate the dark themes of this story outside the confines of the written word.

“Ladies aaaaaand Gentlemen. Are you ready for the match. Of. The. Decade?!!!” Barely heard above the din of the gathered crowd, the announcer boomed the start of the next fight. All around the ring, men and women garbed in black and glittering with insured jewelry settled in their seats; conversations ended in order to watch the prize fight. 

“Get ready to witness the match to end all matches; the fight to win all fights! Two undisputed champions battling it out in the ring for YOUR entertainment. In one corner, six feet five inches and two hundred ninety pounds of muscle and might; the Western Belt Champion, beating over 25 contenders. The Ferocious, the Indomitable, Alpha Ennis!”

“And his opponent. A lithe one hundred eighty-five pounds at just over six feet. With an unprecedented, undefeated streak running over 3 years, nearly 150 matches under his belt. The one, the only, Derek ‘The Wolf’ Hale.”

**** 4 years earlier ****

Derek clutched at the flyer he found pinned to the bulletin board at the halfway house where he was staying now that all the family’s insurance money was almost gone. It had the phone number and contact information for an unsanctioned UFC coach, one John Stilinksi, who claimed to have trained three underground belt-champion fighters. 

Like most red-blooded boys he knew UFC fights were a big time spectacle. He had overheard about other UFC fights, however, in side conversations when he was younger, from his uncle Peter. Never fond of legal pastimes, Peter was always talking about these more clandestine bouts. Derek hadn’t paid them much attention. But, of course, back then he’d had no need to. 

Large sums of money were exchanged in these underground battles for quickly arranged matches. Unsponsored fighters could earn more in one night than a month’s decent work. And with Cora and Laura still in comas from the fire and everything else gone, Derek needed fast money now. Desperately.

**** Present ****

Derek eyed his opponent on the other side of the ring as the opening bell sounded. Ennis snarled, baring his teeth in a primal display of power. Not that he needed to. His biceps alone were the size of Derek’s thighs; his thighs almost the circumference of Derek’s waist. Not for the first time, he felt undeserving of the confidence John had in him. Looking at what he was up against, Derek was grateful for it, however. He was going to be leaning a lot on John's faith in his potential tonight. Knew he had to win to show the man who'd become a sort of surrogate father that he deserved the work John put in him. 

Ennis towered over him by a good half a foot, his body stocky and heavier built. Risking a glance at John hovering close to his corner of the ring, Derek thought he saw resignation in his trainer’s blue eyes. But he couldn’t dwell on it. Ennis took this split-second distraction as an opportunity to lunge at him. 

Derek deftly sidestepped and landed a probing blow to Ennis’s exposed side. Nothing more than a jab to test his opponent. But it was telling that Ennis didn’t show even a hint of feeling it. Derek frowned at the lack of response. Despite their illegal nature, enhancers were banned in these matches. They’d both passed their drug tests; it was supposed to be a clean fight. 

Knowing he was no match against Ennis’s sheer power, Derek’s strategy was to wear him down, to play on his significant advantages of speed and the energy of his youth. Ennis was an older fighter, well into his second decade in the ring. Despite this experience, already Derek could tell, compared to his own, Ennis’s footwork was subpar.

Derek and Ennis circled each other, each watching for an opportunity neither one gave. It was a fairly uninteresting fight before that first time-out call. Whenever Ennis would move to attack, Derek would deftly flit back out of his reach. 

After the end of the round bell sounded, Derek rested in his corner sipping from the bottle John provided. His new mouthguard gave the water a bitter kick but he gulped it down anyway. He knew that if he kept up the routine he had going he’d have another win on his hands. 

The spectators wouldn’t like this match much, but in the end, he was doing it for the money so he couldn’t care less what the audience wanted to see.

“Listen, kid. We’ve got a lot riding on this fight. But I think you’ve got the right idea.” John whispered into his ear as Derek studied Ennis, in the opposite corner. “You’re not going to win in a straight out slug-fest. Stay on your feet and keep on dodging those blows.”

Derek nodded, mouth too full of guard to say anything. 

“Alright, stay hydrated, son.” John pushed the waterbottle at him one last time. Aware of how much more he was suddenly sweating than usual, Derek took one final swig from the bottle before jumping back to his feet and heading to the center of the ring. 

**** 3 years earlier ****

Derek looked out into the darkened hallway. His body buzzed with coiled adrenaline. He heard the roar of the crowd fade as the announcer started to hype them up for the next fight: his fight.

“Son, you’re ready for this.” John stood by his right, hand on his shoulder grounding him to this moment. “Nearly a year preparing for this and I can’t say I’ve ever seen anyone as ready and as naturally talented as you. Win this fight and you’ll be able to walk home with over ten grand.”

“It’s not going to be easy and there’s a lot at stake if you lose, so keep that in mind. I’ll see you on the other side of that tunnel, kid.”

**** Present *****

Four rounds in and neither fighter had landed anything more than brief punches. The crowd loudly made their dissatisfaction known to both. Then, halfway through the fifth round Derek failed to dodge a blow. He saw the signs; read Ennis’s body, anticipating the fake swing and the follow-up upper kick. But he was too slow, oddly unable able to fully shift his weight like usual. 

Ennis’s kick landed and Derek felt his wind knocked out. Luckily his opponent was just as surprised as he was that he’d landed his blow and wasn’t able to capitalize on the resultant brief vulnerability. But this was more than a physical blow to Derek, it rocked him deeply psychologically. He’d been so sure he could outlast Ennis.

But with each passing minute Ennis seemed to be moving slight faster, and his own ability to dodge the onslaught of blows came harder with each panted breath. Derek risked a glance at his coach, hoping to catch his eye and get a time out. But John wasn’t in his usual corner; and the time before they broke according to the clock was more than five minutes. 

Derek took several more hits, barely escaping what would have been a nasty grapple, before the buzzer sounded the end of the round. He stumbled out of the ring towards John, each step leaden. 

“Kid, you have to catch your second wind. I can see you flagging out there.” John pushed the nozzle of Derek’s water past his chapped lips, squeezing a good amount into his parched throat. “I’ve been watching Ennis, and for some reason he’s a little weak on his left back step. Use that.”

Derek nodded at the advice and the short minutes of the break flew by as if they were seconds. The strips of cloth wrapped around his hands felt slippery with sweat. Called back into the stage he was panicked inside, knowing his body was not ready for the next, and final, round. His fear was quickly proven when Ennis almost immediately landed a punch below his 3rd rib that left him gasping. 

This time Ennis didn’t give him an extra moment to recover either. Instead he rushed him without grace. Normally Derek could have easily side-stepped such a bullish charge but he was too slow, his feet moving like they were mired in molasses. Ennis collided and crashed with him to the ground.The older man wasted no time, pummeling Derek’s body with powerful hits, per the rules of this match, landing no blows to his face. 

Derek attempted to fight him off, twisting and bucking his body as it was straddled and pinned by Ennis’s superior mass. He could only block and dodge so many punches. Even more heavy blows landed as Derek writhed, trying to escape. 

It was only with the referee’s intervention that Ennis was forcefully removed and Derek able to stagger back onto his feet. Only the briefest of respite was allowed before the referee left the ring, allowing Ennis to once again rush him. 

****4 years earlier****

“Son, do you know what you’re getting into?” John reclined all the way back in his chair. Concerned blue eyes looked at the young man sitting across the table from him. “I’m not going to lie to you, I think that with a lot of training and that attitude you have right now, I have no doubt that you’ll do well. But from what we’ve been doing… Well, this is a whole different ball game.”

“And there is more to this than fists and money if you really want to go to this next level.. Did your uncle talk about what happens to the losing fighters?”

Derek scrunched his brow and thought back to the overheard conversations. He shook his head every so slightly. “No, sir. But it doesn’t matter. I won’t lose.”

“That’s what they all say, son. But I’ve got to let you know, anyway. There is more than money being exchanged here. Your payout will be big, sure, but the price of losing is steep.

“The winning fighter, and whomever they want, can take whatever liberties they want with the loser. That’s the deal here for these specialty bouts. And it’s brutal. I’m not gonna sugarcoat this son, most of the time for the loser this means getting bent over and taking it up the ass. Not just by the champ, either.”

John sighed seeing the young face before him startle but then go back to stoic. “So, I’m gonna ask you one more time… You sure you want to do this?”

Derek hesitated but only for a moment.

“Yessir.”

****Present****

Derek lay dazed on the ring floor. He heard the shouts all around him; the lights flashing from all sides. The cool mat under him offered a slight soothe to his bruised and bloodied skin. He didn’t know how long he laid there, feeling more than seeing Ennis strutting around him in triumph. Out of the corner of his blurred vision, he swore he saw John off to the side talking with a fuzzy-looking Deucalion, the fight’s manager, and palming a large stuffed envelope.

****Two hours ago*****

John was watching Parrish wrap Derek’s hands when his phone rang. He pulled his cell from his pocket. A sudden sheen of sweat glistened on his brow when he saw who it was. He thumbed the screen to answer with a sigh.

“Yes. I got the package. Are you sure this is the only way? I’m having some second thoughts.”

“No, no of course not. No. I’ll do it. Ennis will win the fight tonight. I understand.”

Twenty minutes later John’s hand struggled to pour the powder in Derek’s water bottle. More than a fair bit had spilled from the narrow spout. 

Biting his lower lip, he thought of his son lying in that hospital; tubes and machines all around him. He prayed Claudia would forgive him for what he was about to do, but it was either this or his son not getting into that trial drug run. And he couldn’t lose the last bit of his family. 

Given Derek’s on situation with his sisters, John figured the kid would come to understand his decision… Eventually.

**** Present ****

Derek struggled weakly against Ennis when wide hands grabbed him and flipped him onto his stomach. 

“Dun touch muh!” His words were slurred, but the shot of adrenaline that hit his system when he realized what was happening went a ways toward clearing his dizzied mind.

He’d lost the match and Ennis was already advancing on his spoils.

Derek’s hands shot out and scrabbled at the mat, unable to find purchase. He tried to crawl out from under the winner’s grasp. He yelled when he felt iron fingers slide under the waistband of his trunks and pull. Rolling his shoulders, he slipped over onto his side, frantic in his attempt to fight Ennis off. His limbs were oddly heavy and uncoordinated though and wouldn’t mind him. 

Derek’s breath hitched in his broad chest at the sound of tearing fabric. His heart pounded faster than it ever had in a fight when his flimsy shorts were ripped off. 

“No... This isn’t right…” He gasped at the bite of straps into his skin. Ennis had his jock between his fingers now and tugged it hard. Derek knew he’d have strap-shaped bruises tomorrow as the nylon cut into his the flesh of his hips and at the base of his asscheeks before finally the bands snapped and his cup was pulled off. 

Feeling his bare ass hit the hot shine of the venue’s lights, Derek shouted, “We’re nah even out of tha ring yet!” He thrashed this way and that, but every movement of his body hurt, bruised from the fight and it was unnaturally heavy to move. 

“Fuck you!” Ennis leaned over and growled in his ear. “You lost. Winner takes all! That’s the rule of this game and you know it!”

A sharp slap to Derek’s ass made him yell. “Look at that gorgeous butt, Hale. Yeah, I’m gonna pop this sweet double bubble of yours. Always told my boss this was your real moneymaker. 

“And tonight I’m going to prove it.”

The rough caress that slid over his spank-warmed skin had Derek shouting just as loud as the slap had. Ennis smiled down at the muscular body trapped beneath his thick thighs.

“Hot damn, ’m gonna love snatching this cherry. Almost as much as this crowd is gonna love watching your undefeated ass meet its match tonight!”

Vice-like hands gripped Derek’s hips and pulled them up, lifting his exposed ass into the air. 

“That’s what you get… Mr. High and Mighty Hale. Refusing to fuck your losers. You think it’s because you're better than everyone else. People say you have morals, but I know it’s because you're just a bitch and tonight I’m gonna prove it!”

Derek blinked to clear his dancing vision. He howled in protest; his voice the only thing that still seemed to worked. 

But his cries were useless. No one was going to stop this. Derek felt the buzz on his skin of the frenzied air around him. Ennis was right. The crowd’s anticipation was palpable and their raucous volume now deafening. 

The whole world fell silent to him, however, when Derek felt spit hit his spread cheeks, a sloppy bullseye on his virgin pucker. His bowels turned to ice when the blunt head of Ennis’s cock butted against his asshole. 

His mind spun, recalling John’s unusual recommendation earlier that day to take an enema so that he “had nothing weighing him down in the ring.”

He cursed himself for being such a stupid idiot and following his coach’s directions

“Staaaap!” Unlike his previous vocalizations, now even his own voice seemed disjointed from his body. His brain, however, was fully aware of everything. At this fresh betrayal fresh tears blurred his vision. 

“You know what happens to losers in the ring.” Ennis’s yelled into his ear. Then he lifted his head and roared to the clamoring crowd’s approval, “Losers get fucked!!!”

Derek’s body was forced once more into the mat. This time driven down by the thrust of Ennis’s dick as it cruelly plumbed into a virgin tunnel. His eyes rolled back in his head at the painful burning stretch of it. It didn’t matter that his bowels were empty, he was seized by the urge to shit. 

While his body screamed internally at its violation his voice screamed out into the cheer-filled air of the ring. 

“Jesus Christ! Thaaaa hurts! Stop!” His pained were cries lost amongst the crowd’s lustfull roars. His own throat, raw from the strain, Derek gave one final howl when Ennis’s fat cockhead before he fell silent.

Fingers fisted into his hair, pulling it up from the centering solidity the floor. Derek’s drugged body rocked from Ennis’s violent thrusts as the champion cored his way into him. Ennis grunted in satisfaction as his dick mined Derek’s tight channel. With every brutal thrust, a sob escaped, driven from Derek’s bitten lips.

“Look at all these people watching you.” A thick tongue roughly licked away the tears from his cheek leaving in its wake a sticky swathe of spit.

“Undefeated.” 

Ennis punctuated his words with cruel thrusts. His balls slapped hard against Derek’s taint, heavy enough to bruise. 

“Unbroken.”

Around them the crowd grew quieter, mesmerized watching the even more brutal battle before them now. A hush fell over the stands athey strained to hear Ennis land the blows of his words.

“Not anymore!” 

Aware of the shift Ennis grew louder. His asscheeks flexed as he pumped his cock deep enough inside him Derek was sure his stomach bulged with each slam.

“After I’m done with your tight asshole.”

“Now my bitch cunt!”

“Everyone is going to see you broken!”

Derek choked on his own snot as his rectum ached and spasmed around the unwanted intrusion. His clenching only made Ennis even more rabid.

“Everyone!” His conqueror bellowed.

“And EVERYONE will have a taste your defeated pussy.”

He’d thought he’d hit the bottom of his anguish but these words proved him wrong. Horrified Derek looked out over the crowd at the kaleidoscope of faces. Even half-blinded by his tears he could see the feral smiles of the audience audience reveling in his humiliation. 

His utter debasement, his body with no more autonomy than a doll’s. His dark head hit the padded fmat with a ‘thunk.’ His naked skin rubbed against the stained floor, slicked with sweat and blood. Derek’s hitching breath was pressed out of his lungs as Ennis slumped over him, his hips never ceasing in their mad pumping.

But Derek could do nothing but lay there, passive, smothered as the champion’s body wholly covered his in its claiming. Ennis’s litany of humiliations was cut off only when he placed the brand of his mouth on Derek’s exposed neck. Biting up and down the gasping throat, marking Derek repeatedly with hickeyed badges of his defeat.

**Author's Note:**

> Special thanks to Always_Bottom_Derek who fleshed out and graced the story with his magic touch. Please read his work and make sure to comment and leave him feedback!


End file.
